Acetic Acid → HCID 69659269, compound

HRID 1829046Notes

Reaction equation

HRID 1829046 reaction equation
[O:1]=[C:2]1[C:10](=[C:11]2[C:19]3[C:14](=[CH:15][C:16]([NH:20][CH2:21][CH2:22][O:23][C:24](=[O:27])[CH2:25]Br)=[CH:17][CH:18]=3)[CH2:13][O:12]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.CC(O)=O.[OH-].[Na+].[NH:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1>>[O:1]=[C:2]1[C:10](=[C:11]2[C:19]3[C:14](=[CH:15][C:16]([NH:20][CH2:21][CH2:22][O:23][C:24](=[O:27])[CH2:25][N:34]4[CH2:39][CH2:38][O:37][CH2:36][CH2:35]4)=[CH:17][CH:18]=3)[CH2:13][O:12]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 8083MorpholineHCID 14798Sodium HydroxideHCID 73734909HCID 73734909, compound

Product 1

HCID 69659269HCID 69659269, compoundYield 51%

Procedure

A mixture of bromo-acetic acid 2-[1-(2-oxo-1,2-dihydro-indol-3-ylidene)-1,3-dihydro-isobenzofuran-5-ylamino]-ethyl ester (35 mg, 0.082 mmol) in morpholine (1 ml) was stirred at room temperature for 1.5 hours. The mixture was poured into 2% AcOH aqueous solution (50 ml) with stirring. The mixture was then basified with NaOH solution. The solid was filtered, washed with water, dried under vacuum to give morpholin-4-yl-acetic acid 2-[1-(2-oxo-1,2-dihydro-indol-3-ylidene)-1,3-dihydro-isobenzofuran-5-ylamino]-ethyl ester as a yellow solid (18 mg, 51%).

Workup

  1. stirringwith stirring
  2. filtrationThe solid was filtered
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-1df14f3f99d84e98aa08128cdd0df886
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

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